What has been your biggest career failure and how have you learned from it?

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Founder/Chairman/CTO in Telecommunication, 201 - 500 employees
From a technical and security standpoint, I've been doing this long enough that I don’t consider the things that happen in the course of doing our job—like breach response—to be lowlights. We try to avoid them, but part of being in this game is becoming resilient to that and figuring out how to respond, learn from things, and move forward.

But from a leadership standpoint, I put a lot of stock in my team and the people that I've brought into Bugcrowd, and there were different points in time where I didn’t do as good a job of directing what they were doing, or meeting their expectations as I should have. I did start off the organization as CEO—I did actually go to the board about four and a half years in and talk to them about getting some grown ups in the room.

That was mostly because I recognized that I was stretching my ability to learn on the fly, and that was doing a disservice to the team and to the market itself. So in hindsight, a lowlight would be the things that contributed to putting me in that position. I have no regrets around that decision itself. But it’s something I try to avoid in the future. It's a sensitive topic, but one that's good to talk about because you don't often hear these stories told, so I do try to share a little about that.
CISO in Software, 501 - 1,000 employees
I'm a psychologist as well as a security professional, and we're supposed to be able to read people really well, but in a previous business I worked in, I hadn't been involved with a certain area of the business. After we’d done a security analysis, I was feeding the results back to the exec group, but I hadn't realized the particular personality of one of the senior executives. When this exec got bad news about things happening in his area, he took it personally and tried to shift blame in other places. Because I was delivering the report, it got shifted back to me. I ended up in tears. I had completely misread that situation. I managed to get those relationships back on track, and once I understood how this person worked, I could be more strategic with them. That was definitely one of my failings. And I've had heaps.

Another one happened at a different organization, when I was just starting to get into my extracurricular, social media thought leadership, communicating in a really open way—not about work, just about digital transformation and digital culture. And I found out that the organization wasn't keen on me doing that. They didn't see it as a good thing, or a new way of communicating, and I ended up getting taken out in a restructure because I didn't fit with the other people. I was too different.

But if you don't fit in, it's actually good to move on in those situations. I ended up where I am now in Kordia and I love it. And they hired me because they really wanted someone who could front foot that stuff. At the time, it really felt like I'd failed in some way. But it was just that the environment wasn’t conducive for me any more because I was doing different things, and behaving unlike other people in the organization.
VP, Director of Cyber Incident Response in Finance (non-banking), 10,001+ employees
I'd like to think that I've made a career out of failing. I once managed a $3 million capital project that was failing, and got a promotion out of it. But my most epic failure that actually had a negative impact on my career, happened when I was a project manager at Intel. I was asked to give an update to the Director of the Engineering Computing Program and was given two weeks to put everything together. I spent a couple of days doing word vomit: I put all of my candid thoughts into PowerPoint and set it aside.

And then I put together the management PowerPoint presentation. It was professional and had everything you would want to see in an executive-level presentation. I sent my slides off the night before. The management team were all in California and I was in Oregon, so the next day I sat down in a conference room and got on the call. This was more than 20 years ago, so there was no Zoom and no screen sharing. I got through my piece of the presentation and when they paused for questions, a guy pipes up and says, "Yeah Jeff, my name is so-and-so. What do you mean that my team is not participating?" My word vomit slides were the ones that I sent to the executives—I had egg on my face like you could not believe.

And they said, "Well, let's just go through the rest of the presentation." I said, "Can we not? You don't have the right slides, you don't want to see what's left." But we wound up going through the rest of the presentation and the next day I was pulled off of that project as the lead. Seven years later, the Director to whom I had given this presentation was coming to visit us. As the AV geek, I was in the conference room setting everything up. My general manager (GM) walked in with the Director, introduced me, and the guy said, "Oh, I know who Jeff is." Seven years later, he still remembered that screw up.
Global CIO & CISO in Manufacturing, 201 - 500 employees
Early on in my development career—about 20 years ago before I had any good management software—I had an app that was internationally recognized. I was coding all day long. One of the key features the tool had was system clean up. Of course, I have to run this, test it, and debug it. And this is hours of time. I hit run to test that it functioned, and it was taking a lot longer than it should. Normally it should just delete the files and go.

I had a pathing issue: it started at the root, and it was deleting and eating up everything. This was Windows, so it ate quite a few Windows folders. It ate part of my code base. I had to restore from backups from two days prior. It took about a week for me to recover emotionally before I went back to coding, pulling in libraries that I had updated, and looking at what I had done because now there was a mismatch across some of the codes. That was definitely a lowlight.

A little while after that, I pretty much gave it up and said, "I'm not doing that again." Now I say to folks, "If you are not backing up your stuff, you better take a second glance at everything." I don't care how much CPU something takes, I would rather get a faster computer with two or three redundant backups and source control, etc., than have to go through that again.
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Founder/Chairman/CTO in Telecommunication, 201 - 500 employees

It feels like one of those mistakes that everyone makes twice. And then never again after that.

Director of IT in Construction, 1,001 - 5,000 employees
I have done countless mistakes and said seriously dumb things, but the one that I learned the most from was telling a developper that he did a shit job.

Many years ago, I had this PM/BA/QA role in a small custom dev firm and was testing out a new feature our top dev had been working on for a while. 

The feature did not work, at all, basically crashed instantly whatever you did. I was furious, I could not understand how so much work had been done and so little was functional. We were on a tight deadline, and I was mad, so I let my emotions get the better of me. I went to see the dev and told him, in a very frustrated and negative tone, something along the lines of "that feature you did is totally out whack, did you even test it before sending it over?" 

Boy was he pissed. I remember exactly where I was, where he was, in which room it happened and almost the time of day.

And he was right to be mad at me. I was completely out of line. I had attacked his work and was completely unprofessional.

If I had just said "I was testing the feature X and got an error message while doing Y", he would have leaped on his keyboard, skipping lunch and anything in between just to fix the error and I would have gotten a perfectly working build before leaving the office.

I know it sounds silly to senior leaders now, and I chuckle a bit when people tell me they have a hard time with their team when they bring them issues the way I did. 

Words are extremely important, much more than I thought back then. A simple inflex in intonation and swapping 5 or 6 words in a sentence can make the difference between someone being horribly mad at you or genuinely engaged into completing/fixing what needs to be done.

The story ended well. I recognized my mistake, gave sincere apologies, explained the issue factually, and got a perfectly working build briefly after he found the cog in the wheels.

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We provide company-wide training56%

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I am unsure how we handle security training.3%




Yes, but not enough, we want/need to ramp up38%


No, but I expect this will change soon6%


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